Short nonbond and long C-C bond in naphthalene-1,8-diylbis(10- methylacridinium) and the corresponding hexaphenylethane derivative: A new electrochromic pair exhibiting dynamic redox properties

Hidetoshi Kawai, Takashi Takeda, Kenshu Fujiwara, Takanori Suzuki

Research output: Contribution to journalArticlepeer-review

35 Citations (Scopus)

Abstract

The extremely long C-C bond [1.696(3) Å] in the colorless dispiroacenaphthene-type hexaphenylethane is cleaved readily upon electrochemical transformation into the orange colored naphthalene-1,8- diylbis(acridinium), in which the two cationic units are forced to overlap in a face-to-face manner exhibiting the shortest C + ⋯C + interatomic contact of 2.927(7) Å among the values ever reported.

Original languageEnglish
Pages (from-to)8289-8293
Number of pages5
JournalTetrahedron Letters
Volume45
Issue number45
DOIs
Publication statusPublished - 2004 Nov 1
Externally publishedYes

Keywords

  • Acridan
  • Acridinium
  • Carbocation
  • Hexaphenylethane
  • Long bond
  • Short contact
  • peri-Interaction
  • π-π Interaction

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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